Every sales organization has the right ingredients for success: reps who are hungry to learn and hit quota, managers who are the force-multipliers leading those reps, sales enablement that supports your team with training and content, and a sales coaching program that holds everyone accountable to constant improvement. 

Sounds like a recipe for success, right? Objectively, yes. But without the right binding agent, none of it sticks. Research shows that sales managers carry a lot of this responsibility—yet 70% of initiatives fail due to ineffective delivery by middle managers. Why? A lack of manager enablement.

I recently spoke with Kate Michalowski, GTM Enablement Manager at Melio; Jason Ross, VP of Sales at Jobber; and Malia Di Salvo, Sr. Manager of Sales Coaching at Upwork to discuss how we can better enable and measure manager success. We identified 5 non-negotiable coaching metrics every org should be tracking, but at the core of those metrics is the true binding agent for sales success: a culture of coaching. 

Click here to watch the webinar on-demand

Coaching isn’t a one-time event. It’s an ongoing process that does more than improve sales effectiveness—it permeates our culture, and this elevates our potential. So how do we build and sustain this type of culture? Here are several key takeaways from our conversation you can use to start building a culture of coaching right now.

>>> Looking to improve your coaching culture? Download our coaching playbook for promoted reps, sales managers, and enablement leaders here. <<<

1. Invest in manager enablement

This begins with reframing the manager role, because a manager’s primary job is to be a coach and mentor. They’re not simply “managing” people. Properly enabling them means ensuring they understand that responsibility. 

Next, we need to provide them with sales coaching software that clearly defines what success looks like and allows them to easily document and track performance. How many coaching activities should they complete? How should they document those coaching moments? How will their success be measured? 

Finally, we must coach our sales coaches. We talk a lot about coaching sales reps, but our coaches need coaching, too, and we can’t let them go it alone just because things are going well. Sales managers juggle a lot every day, and we must provide them with the support they need to carry out initiatives while developing their people. 

“The manager's job is coaching and enabling people to do the best work that they can. Of course, it’s important for us to measure things like coaching quality and quantity and have some process and formality around coaching. But we have to start with a culture of coaching and set those expectations for what it means to be a people leader.” Jason Ross, VP of Sales, Jobber

2. Get org-wide buy-in on initiatives 

When it comes to defining and executing on OKRs, we have to remember that our sales managers and reps are the ones carrying out day-to-day activities that help us collectively hit goals—but more often than not, reps don’t really care about your OKRs. They care more about their paycheck, and it’s not always easy to see how the two tie together. 

Your sales enablement function can help bridge the gap between a rep’s focus area and high-level business goals by connecting OKRs to things like quota attainment and team participation. To see those initiatives come to fruition, reps and managers need to know what’s in it for them, and it’s up to us to communicate this. When they’re able to see why OKRs matter for them on a personal level, they’re more bought in and will execute more effectively to help you hit those goals. 

“Ask your reps: How do you see this initiative benefitting your book of business, your customers, your paycheck? How will you utilize this? I’ve found that that gets so much more leverage when you’ve involved someone in that conversation. And, a lot of times, they bring up things that we would otherwise miss, because we’re not as close to the customer.” Kate Michalowski, GTM Enablement Manager, Melio

3. Take a progressive approach to coaching

Coaching is not an isolated event, and we can’t measure it that way. The results aren’t always obvious or immediate. We must define efficacy metrics progressively from the outset of any coaching initiative, even before we see how it directly impacts the sales process. 

This starts with how well people receive coaching and training. What’s the overall sentiment? Did the training resonate? Was the material communicated in an effective way that people understand? While we strive toward a North Star metric or desired result, we have to make sure we lead people toward that effectively. 

A true measure of coaching quality is when we start to see and hear the material being coached on in action. Even if managers or reps are employing a new skill, messaging, or content, the quality of coaching depends on whether or not those things work. Measuring success progressively means taking into account how successful that material is out in the field and iterating as needed to achieve desired results. 

“I love the saying for coaching, ‘You don’t do it until they get it right. You do it until they can’t get it wrong.’ That’s why you can’t just have a fly by coaching session. You have to make sure you have a progressive way of measuring that quality of coaching, and if that’s not working, you can quickly pivot and adjust your approach to make sure that changes and any iteration happen quickly.” – Malia Di Salvo, Sr. Manager, Sales Coaching, Upwork

Improve Sales Effectiveness with a Culture of Coaching

This conversation was loaded with insight, ideas, and strategies to help sales leaders create coaching cultures. Watch the full webinar on-demand to hear it all—or get in touch with us here to learn how sales coaching software can help you lay the foundation for a culture of coaching. 

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